Location: Western Massachusetts, along the New York border Description/Highlights/Points of Interest After a landslide in 1990, a giant face appeared on the mountain; a face the citizens believe is Old Chief Greylock. The mountain, called Mt. Greylock in respect to this historic man, is the highest point in Massachusetts. To make this spot even higher, an uniquely-shaped lighthouse is positioned on the top that can be seen from 70 miles away. Mt. Greylock has other interesting aspects. Standing on the peak, one has a matchless opportunity to view a fantastic panorama of five states. Furthermore, authors like Henry David Thoreau, Herman Melville, Nathaniel Hawthorne, Edith Wharton, William Cullen Bryant and Thomas Cole received inspiration gazing at this large mountain. Suggested Itinerary Check back soon for a sample itinerary!